4-(2-formylphenyl)dibenzothiophene | 485824-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4-(2-formylphenyl)dibenzothiophene
• 英文别名: 2-dibenzothiophen-4-yl-benzaldehyde；2-Dibenzothiophen-4-ylbenzaldehyde
• CAS: 485824-13-3
• 化学式: C₁₉H₁₂OS
• 分子量: 288.37
• InChiKey: WJNPVCBDJVKTDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基碘化锍 、 4-(2-formylphenyl)dibenzothiophene 在 氢氧化钾 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 4-(2-epoxyethylphenyl)dibenzothiophene
  参考文献：
  名称：

  Synthesis of Dihydrodiol Metabolites Implicated in the Mechanism of Carcinogenesis of Phenanthro[4,3-b][1]benzothiophene and Phenanthro[3,4-b][1]benzothiophene, the Polycyclic Sulfur Heterocycles with a “Fjord” Structure

  摘要：

  Dihydrodiols, which are potential proximate carcinogens of phenanthro[4,3-b][1]benzothiophene (3) and phenanthro[3,4-b] [1]benzothiophene (4) and possess a "fjord" structure, were synthesized. The dihydrodiols synthesized were trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b] [1]benzothiophene (5) and trans-3,4-dihydroxy-3,4-dihydrophenanthro [3,4-b] [ 11 benzothiophene (6). The precursors to the dihydrodiols 5 and 6 were 3-methoxyphenanthro[4,3-b][1]benzothiophene (11) and 3-methoxyphenanthro[3,4-b][1]benzothiophene (16). Compound 11 was obtained via Suzuki cross-coupling reaction of easily accessible starting materials. However, this synthetic strategy utilizing Suzuki reaction for the preparation of 16 was comparatively less productive than that described previously due to time-consuming synthesis of the starting material(s), and extremely poor yield associated with cyclization of the epoxide 15 to 16. The methoxy derivatives 11 and 16 were converted to the corresponding dihydrodiols 5 and 6 by a sequence involving demethylation, oxidation, and reduction. The trans-stereochemistry of the dihydrodiols was established by H-1 NMR, which indicated a large coupling constant between vicinal carbinol protons. The UV spectra of the dihydrodiols 5 and 6 are presented.

  DOI：

  10.1021/jo020493l
• 作为产物：
  描述：

  二苯并噻吩-4-硼酸 、 邻溴苯甲醛 在 [Pd(C₃H₅)Cl]2/Tedicyp complex potassium carbonate 作用下， 以 xylene 为溶剂， 反应 20.0h， 以92%的产率得到4-(2-formylphenyl)dibenzothiophene
  参考文献：
  名称：

  钯/四膦催化杂芳基硼酸与芳基卤化物的铃木交叉偶联

  摘要：

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化杂芳基硼酸与芳基溴化物的Suzuki反应，以及芳基硼酸与杂芳基的偶联溴化物。噻吩或苯并噻吩硼酸，呋喃或苯并呋喃硼酸和3-吡啶硼酸与各种芳基溴的偶合得到相应的偶合产物，收率很高。然而，在大多数情况下，使用杂芳基溴化物与芳基硼酸进行的逆反应在底物/催化剂的比例方面获得了更好的结果。

  DOI：

  10.1002/jhet.5570450109

文献信息

• NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
  申请人：SFC CO., LTD.

  公开号：US20180072753A1

  公开（公告）日：2018-03-15

  The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R 1 to R 8 , and R 11 to R 20 are as defined in the specification.

  本发明涉及一种由[化学公式A]表示的有机发光化合物以及一种有机发光器件。在化学公式中，A、X、Y、Z以及取代基R1至R8和R11至R20如说明书中所定义。
• Palladium/tetraphosphine catalyzed suzuki cross‐coupling of heteroarylboronic acids with aryl halides
  作者：Isabelle Kondolff、Henri Doucet、Maurice Santelli

  DOI：10.1002/jhet.5570450109

  日期：2008.1

  ne/[PdCl(C3H5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- or benzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化杂芳基硼酸与芳基溴化物的Suzuki反应，以及芳基硼酸与杂芳基的偶联溴化物。噻吩或苯并噻吩硼酸，呋喃或苯并呋喃硼酸和3-吡啶硼酸与各种芳基溴的偶合得到相应的偶合产物，收率很高。然而，在大多数情况下，使用杂芳基溴化物与芳基硼酸进行的逆反应在底物/催化剂的比例方面获得了更好的结果。
• Synthesis of Dihydrodiol Metabolites Implicated in the Mechanism of Carcinogenesis of Phenanthro[4,3-<i>b</i>][1]benzothiophene and Phenanthro[3,4-<i>b</i>][1]benzothiophene, the Polycyclic Sulfur Heterocycles with a “Fjord” Structure
  作者：Subodh Kumar

  DOI：10.1021/jo020493l

  日期：2002.12.1

  Dihydrodiols, which are potential proximate carcinogens of phenanthro[4,3-b][1]benzothiophene (3) and phenanthro[3,4-b] [1]benzothiophene (4) and possess a "fjord" structure, were synthesized. The dihydrodiols synthesized were trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b] [1]benzothiophene (5) and trans-3,4-dihydroxy-3,4-dihydrophenanthro [3,4-b] [ 11 benzothiophene (6). The precursors to the dihydrodiols 5 and 6 were 3-methoxyphenanthro[4,3-b][1]benzothiophene (11) and 3-methoxyphenanthro[3,4-b][1]benzothiophene (16). Compound 11 was obtained via Suzuki cross-coupling reaction of easily accessible starting materials. However, this synthetic strategy utilizing Suzuki reaction for the preparation of 16 was comparatively less productive than that described previously due to time-consuming synthesis of the starting material(s), and extremely poor yield associated with cyclization of the epoxide 15 to 16. The methoxy derivatives 11 and 16 were converted to the corresponding dihydrodiols 5 and 6 by a sequence involving demethylation, oxidation, and reduction. The trans-stereochemistry of the dihydrodiols was established by H-1 NMR, which indicated a large coupling constant between vicinal carbinol protons. The UV spectra of the dihydrodiols 5 and 6 are presented.